


"The Bet"

by BerylSpring



Category: Supernatural
Genre: F/M, Foot Massage, Graphic Depictions of Sexual Activity, Hair-pulling, Moose Sam, Motel Smut, One Shot, Oral Sex, Playful Dean, Rough Sex, Smut, Teasing, Tickling, Vaginal Fingering
Language: English
Status: Completed
Published: 2015-12-04
Updated: 2015-12-04
Packaged: 2018-05-04 20:55:18
Rating: Explicit
Warnings: Creator Chose Not To Use Archive Warnings
Chapters: 1
Words: 3,505
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/5348228
Author URL: https://archiveofourown.org/users/BerylSpring/pseuds/BerylSpring
Summary: <blockquote class="userstuff">
              <p>Maggie had been hunting with Sam and Dean for a few months, but this is the first night they all had to share a hotel room.  A game of rock, paper, scissors landed her a spot in Dean’s bed.  Dean decides to play some more games when Sam falls asleep.</p>
            </blockquote>





	"The Bet"

**Author's Note:**

> My first one-shot so be gentle. Thanks for reading!

Maggie stretched her legs out in the back seat of the Impala. She and the Winchesters had just cleared out a nest of vampires on the edge of town, and her muscles were a bit sore. It had only been about three months ago that they all met working the same case, but they had hit it off. Sam and Dean had become somewhat like family to her, like the two older brothers she never had. Unfortunately, sometimes brothers were a pain in the ass.

“Get your dirty boots off my backseat, Magpie!” Dean ordered, turning around to look at her.

Maggie whined, “Oh but Dean, my legs hurt!”

“They’re gonna hurt if you don’t move them,” He said, playfully swatting at her ankles.

She gave him her best pouty face but he wasn’t having it, “Fine. God, you are so obsessed with this car!”

They were parked at the Wigwam Motor Court waiting for Sam to come back with their room keys. It was already pretty late, and there were a bunch of cars parked in the lot already. Hopefully they had a couple of vacancies left because she did not want to get back on the highway and find another. She was beat. A few minutes later, Sam came bounding down the front office steps on his moose legs and back to the car.

“They only have one room left, so I took it,” he said sliding in to the passenger seat, “it’s down on the far end there.”

“That okay with you sweetheart?” Dean asked, looking at her in the rear view mirror.

Maggie shrugged, “Yeah, that’s fine. I just want to get cleaned up and get some sleep.”

With that settled Dean pulled his Baby around the center island and cruised down to the very end of the building. They parked right in front of their door and started grabbing their overnight bags from the trunk. Maggie shoved her bag into Dean’s chest and told him to be a dear and carry that in, and then grabbed the key out of Sam’s hand, making a beeline for the door. Sam laughed at the look on his brother’s face when he realized what she was doing. The three of them had gotten a little more than messy taking the heads off of those vamps and they were all clamoring for a shower. Maggie anticipated that and assured herself the number one spot on the roster.

When Maggie finished her shower she came out wrapped in a towel, with another wrapped up around her long brown hair, keeping it out of the way. She figured after the stunt she pulled Dean wasn’t going to be nice enough to bring her bag to the bathroom for her so she could change into her pajamas, so she padded across the floor confidently in her bare feet to retrieve it herself. She ignored the stares the boys were giving her. It wasn’t like she didn’t know how short the makeshift cover-up was, she knew they were going to check her out. Let ‘em stare! She even wiggled her butt a little on her way back to the bathroom.

“Like what you see boys?” she teased.

She closed the door behind her, changed into a pair of sweats and a blue tank top, and piled her hair up in a messy bun at the back of her head before offering up the bathroom to the guys. Dean took a shower next, and then Sammy took his. They all felt so much better afterwards that they decided to stay up a little before going to bed. It was amazing what a nice hot shower could do to refresh you.

A game of poker was in order, so Dean grabbed a six-pack that he had in the trunk of the car and Sam went to fill the ice bucket so they could cool them down a bit. They each had a couple of beers, and Maggie whipped both their asses at cards. They didn’t know her dad was a professional poker champion back in the day and had taught her a few things. She thought it was funny when Dean got all bent out of shape about losing to a girl.

“I’m pretty sure that means you have to rub my feet, Dean,” she joked, they hadn’t actually bet anything, but to her surprise he lifted her feet into his lap and started massaging. His hands were strong and he actually was doing a pretty good job. He stopped just as she was starting to relax.

“Hey!” she protested.

“That was just a free sample, you gotta pay for the rest,” he winked at her and got up to yawn and stretch.

Maggie got up to stretch too and asked, “What bed do you all want?”

“What?” Dean asked incredulously, “I ain’t sleeping with him!”

“Dean it’s not a big deal, Maggie should have a bed to herself,” Sam argued in her defense.

“Well, you’re a big deal, and by big I mean huge. She’s little, so you two can share.”

Maggie held back a laugh and egged Dean on, “What makes you so special that you get your own bed?”

Dean scoffed, “Uh, cause I’m the oldest.”

“No, no, no,” she refuted, “that is _not_ a rule.”

“Only way to settle it fairly is a game of Rock, Paper, Scissors,” Sam offered.

Maggie and Dean looked at each other and then back at Sam. That seemed reasonable. Honestly she didn’t really care if she had to share with one of them, as long as she had a bed to sleep on. They decided that the loser of the first round was out and automatically sharing with someone, and the winner of the second round got the bed to themselves. Dean lost the first round and was sour about it.

“Alright ready,” Sam said, starting the next round.

Sam’s paper beat Maggie’s rock. Sam chuckled in victory.

“I thought you were championing my right to the bed?” Maggie asked.

“Sorry, Mags,” Sam said as he climbed into the bed closest to the door, “I don’t really want to sleep with him either.”

Dean gave her a pat on the ass before jumping into their bed, “C’mon sugar, it’s you and me!”

Sam started laughing at her, and Maggie couldn’t help but chuckle too, “You’re both dicks!”

Maggie climbed into bed next to him and burrowed herself under the covers. Dean shook his head and reached over her to turn of the bedside lamp, plunging the room into darkness. Sam said goodnight and rolled over on his side, turning his back to them.

“Goodnight, Magpie,” Dean announced as he rolled onto his back to get comfortable.

She was on her side with her back to him as well, “Night.”

It always took her a few minutes to get comfortable enough to settle down, and she kept wiggling in her spot on the less than stellar mattress to try and find a space where there wasn’t a spring poking into her skin. She heard Dean huff behind her.

“Sorry, I’ll settle down in a minute.”

A minute passed and she had to move again. Maybe if she turned over she’d be more comfortable. The bed bounced with her movement.

“You okay there?” Dean asked mockingly, “Are you having a seizure? Do you need to bite down on something?”

Maggie laughed and punched him lightly on the shoulder, “Shut up and go to sleep!”

“Both of you shut up,” Sam called from the other bed, bringing about fits of laughter from the two of them.

They lay there face-to-face for a long while; Dean even started to snore lightly for a bit. Sam had fallen fast asleep too, but Maggie still wasn’t comfortable. She twisted and turned a few more times, waking Dean from his temporary slumber.

“Maggie,” he said gently circling his arm around her waist and pulling her close, “just relax and go to sleep.”

He nuzzled his face against her neck and spooned her. She tensed for a minute at the intimacy of it all, but his body felt warm and comfortable cradling hers so she allowed herself to sink into him. This was new and different. She always thought both the Winchesters were attractive, but she never really felt anything more than friendship towards them. She actually thought this was kind of nice and sweet. She hadn’t really seen this side of Dean before.

“Your hair smells good,” he muffled into the back of her neck. Little shivers ran up her skin.

“That’s because I’m awesome,” she joked to cut the sexual tension that had suddenly filled the space around them.

Dean sniggered and started tickling her ribs, “Smartass.”

Maggie jumped and tried to twist out of his grasp, but he kept scrunching his fingers into her side. She was giggling and protesting loudly. He stopped his pinching and smoothed his hand down her side.

“Shhhh,” he said laughing, “you’ll wake Sammy.”

She turned towards him and smacked him again, “That’s cause your being a dick.”

“Oh really!” he exclaimed in a hushed tone before pretending to poke at her ribs again.

“Stop!” she giggled back at him, grabbing his hand in defense.

His fingers lingered on hers, squeezing them between his own. There was just enough light seeping through the crack in the curtains to see each other’s features in the darkened room. She smiled at him and he brought his hand back up to her ribcage. She flinched for a second thinking he was going to start again, but he just ran his hand up and down her side. They looked into each other’s eyes for a moment before he smirked at her.

“What?” she asked.

Instead of responding he pulled her body into his quickly, chest-to-chest, and began gingerly kissing her lips. Forgetting any and all apprehension, she kissed him back fervently, lightly running her tongue over his bottom lip. Dean let out a throaty moan and tangled his fingers up through her hair, giving it a tug, as he pushed his tongue into her mouth. Maggie brought her hand to his hips and dug her fingertips in, gently squeezing. She could feel him getting hard between them, his cock growing engorged against her belly.

“Dean,” she whispered, as he brought his lips down her neck to nibble at her skin, “what are we doing?”

He answered in between each kiss that he placed on her neck and shoulder, “I don’t know about you, but I’m making good use of your sexy ass body.”

Dean continued to trail kisses down to her cleavage and he slid his hand up under her tank, tenderly massaging the flesh there on his journey up to her breasts. He flicked his thumb over her hardened nipple and then rubbed around it in a circle teasing and tightening it further. Maggie let out a hard breath at the sensation. His hand cupped her left breast and kneaded it roughly, sending pulses of pleasure down to her core.

They heard Sam roll over and groan in his sleep, putting the action on pause for a moment, until they heard him snoring again.

“We shouldn’t do this with Sammy in the next bed,” Maggie protested, but she really didn’t want this to stop.

Dean leaned up on his elbow and smiled at her, “How ‘bout we make this interesting?”

“Oh God, what?” she responded nervously.

He began running his fingers lightly, tickling down her cheek and neck and arm, making her close her eyes and breathe deeply.

“I’m gonna do my best to pleasure you in every way possible, and all you have to do is control yourself enough that you don’t wake Sammy.” He began, “If you do, I get to watch you wash Baby in a little string bikini.”

She chortled, “And if I don’t?”

“What do you want?”

She thought for a second, “I get to drive Baby anywhere we go, for the next week!”

Dean grimaced at her, not sure he liked that deal, but he was confident enough that he could make her wake the dead, so he agreed.

“Deal,” he said and sealed it crossroads style with a deep kiss.

In one swift motion he rolled her onto her back and began climbing down her body, pressing his lips to the skin above the waistband of her sweats. He curled his fingers under the elastic and tugged teasingly as he ran the tip of his tongue across her tender flesh. Maggie undulated under his touch, her skin prickling from the cool air that hit the moist trail he left behind. Sliding his fingers up her sides, bringing the fabric of her tank top with him, he watched her as she writhed under his touch. She was so damn sexy! He placed a light kiss on her forehead before removing her shirt, she didn’t have a bra underneath and he couldn’t help but attack her exposed breasts.

He brought his mouth down around the right one, gently massaging the left as he alternately suckled with hot breath and then blew air between his lips to cool it. He could feel her hands tug on the hem of his tee-shirt, so he sat up and peeled it off exposing his muscular chest. Maggie ran her hands up his skin as he went back to his task, switching to the other breast and repeating his actions. Once he had elicited a few quiet moans, he stopped what he was doing and looked into her eyes.

“Are you ready to take it up a notch?” he said with a devious smile.

Maggie nodded her head and bit her lip in anticipation, eliciting a moan of her own out of Dean. She laid her head back and closed her eyes again at the sensation of Dean’s lips and fingers trailing lightly down her body. When he got to her waistband again, he slowly pulled her pants down her thighs, lifting her butt off the mattress to get them out from under her. She helped him by lifting one leg at a time as he languidly removed the cloth from each one until she was just in her little cotton panties. Lust filled his hazel eyes as he smoothed his hands back up her legs to the object of his desire. Dean traced his fingers across the fabric covering her sex, and he could feel the moisture seeping through.

“Mmmm,” he let out as he rubbed circles with his middle and third fingers, “I can’t wait to taste you.”

Maggie inhaled sharply as he continued to massage her through her wet panties. He smiled taking pleasure in what he was doing to her. She grasped his hand in hers and guided his fingers under the cloth to her sensitive bits and he continued to rub up and down her wet lips, sliding in between her folds. She was doing her best to be quiet, he could tell, but he wasn’t going to lose this bet so he stopped going easy on her. He glided his two fingers to her opening and moved them in slowly, getting a feel for her, stretching her walls with his ministrations. Her breathing quickened as his rhythm did, his fingers pumping in and out of her briskly. A moan escaped her lips and Sam stirred again. Dean laughed quietly as she brought the pillow over her face to muffle the sound.

Pulling his fingers out, she removed the pillow to see why he stopped. He placed both fingers in his mouth, sucking her juices from them and smiling down at her. Dean waited for a minute, letting her stew; amused by the silent temper tantrum she was pulling at the loss of his touch. He winked at her before pulling her panties off, her beautiful pussy finally in view. His dick was so hard right now, but he had to bring her to the edge before he could satisfy himself.

Dean stood at the edge of the bed and wrapped his arms around her legs, pulling her hastily to the end of the mattress. She let out a small yelp in surprise and then covered her mouth, turning her head to make sure Sam was still asleep. When she turned to look back at Dean he was down on his knees on the floor below the foot of the bed with his arms wrapped around her thighs, spreading them open and holding them in place. Maggie took a deep breath in anticipation of what he was about to do. She squeaked a bit when his tongue flicked across her clit and then circled back around to suck gently at it. Dean couldn’t hold in his own moans as he tasted her, licking a trail from her ass to her clit once more. He continued to work his tongue into her folds and her wet opening, working her up until he was sure she would cum. And she did spectacularly, her body vibrating and twitching beneath his mouth. But to Dean’s chagrin, she managed to keep quite.

No more Mr. Nice Guy!

He got up and climbed back over her, nudging her to slide back up further on the mattress. Kneeling upright, he slid his own pants down, kicking them off. They flew over to Sam’s bed, landing on the blanket covering his big feet. Dean’s breathe caught in his throat and Maggie smiled and pointed up at him.

“If you wake him, I win,” she reminded him.

Dean looked back down at her with a sneer, “Yeah, that’s not going to happen.”

Maggie watched as he finally pulled off his boxer-briefs, his rock hard member bobbing up and down with the motion. She involuntarily licked her lips, and Dean took notice looking down at himself and back up to her with pride. He leaned in to kiss her tenderly, one last time before lifting her legs up over his shoulders and pushing his way inside her. She gasped at the feeling of his cock filling her, her walls forming around his girth like memory foam. Dean’s mouth opened at the feeling of finally attending to his own arousal.

If there was one thing Dean Winchester knew how to do, it was to please a woman. Slowly and methodically he began the erotic push and pull, sliding down deep inside her and then backwards again until just the tip of his cock was inserted. The sensation was mind-numbing and Maggie’s body tingled with little pinpricks of delight. The muscles in her stomach began coiling like a snake, waiting for its moment to strike in a wave of pure pleasure. He continued this motion, over and over, gradually speeding up his actions until he was thrusting into her at a good pace.

Maggie arched her back as his head brushed up against her g-spot, the snake constricting further in her belly. The sounds of skin slapping against skin broke the quiet, and for a moment she let herself forget where she was, letting a loud moan escape her lips. Dean smiled and continued his movements, but he leaned closer into her, pushing her legs back towards her head, and allowing for better and deeper access. His rhythmic thrusts began to get faster and harder, until even he had to groan a little from the sensation of her slick folds sucking at his manhood.

“Dean,” she breathed out in a whisper, “I’m gonna…”

He continued his now furious pace grunting as she closed around him tightly, choking his erection with glorious friction. Their labored breathing in sync with one another, he took one last forceful thrust that sent her over the edge. A dam broke inside her wetting him, her walls pulsing around him.

“Oh God, Dean!” she screamed out.

Sam shot up from a deep sleep, pulling the gun from under his pillow and aiming it in the direction of the sound, just in time for Dean to pull the trigger on his load; his hot, sticky seed filling her as he let out a guttural growl.

“Oh my God!” Sam said, seeing his brother’s naked form twisted into Maggie’s and turning his head away from the sight.

After Dean caught his breath, he announced, “That’s what she said.”

Maggie brought her hand up to her mouth a look of embarrassment and amusement mingling on her face. She closed her eyes in defeat as Dean rolled off of her onto the other side of the bed, pulling the covers up to conceal their naked flesh.

“I hate you both!” Sam said, replacing his gun under his pillow and rolling back over to build an imaginary wall between him and them. He was going to have to scour his brain with a Brillo pad to get that horrifying image out of his mind.

Maggie couldn’t help but laugh, until Dean rolled over and looked at her with his most serious face.

“So, what color bikini are you going to wear?”


End file.
